WO2009045489A3 - Process for the synthesis of cmhtp, a paliperidone intermediate - Google Patents

Process for the synthesis of cmhtp, a paliperidone intermediate Download PDF

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Publication number
WO2009045489A3
WO2009045489A3 PCT/US2008/011433 US2008011433W WO2009045489A3 WO 2009045489 A3 WO2009045489 A3 WO 2009045489A3 US 2008011433 W US2008011433 W US 2008011433W WO 2009045489 A3 WO2009045489 A3 WO 2009045489A3
Authority
WO
WIPO (PCT)
Prior art keywords
cmhtp
methyl
synthesis
paliperidone
pyrido
Prior art date
Application number
PCT/US2008/011433
Other languages
French (fr)
Other versions
WO2009045489A2 (en
Inventor
Santiago Ini
Yaron Shmuely
Original Assignee
Teva Pharma
Santiago Ini
Yaron Shmuely
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Teva Pharma, Santiago Ini, Yaron Shmuely filed Critical Teva Pharma
Publication of WO2009045489A2 publication Critical patent/WO2009045489A2/en
Publication of WO2009045489A3 publication Critical patent/WO2009045489A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention provides a process for 3-(2-chloroethyl)-6,7,8,9- tetrahydro-9-hydroxy-2-methyl-4H-pyrrido[1,2-a]- pyrimidin-4-one (CMHTP), comprising reacting 3-(2- chIoroethyl)-2-methyl-9-hydoxy-4H-pyrido[1,2-a]pyrimidine-4-one (CMHP) and/or 3-(2-chIoroethyi)-2-methyl-9-benzyIoxy-4H-pyrido[1,2-a]pyrimidine-4-one (CMBP) with a hydrogen source and at least one hydrogenation catalyst to form CMHTP, wherein the hydrogen source is cyclohexene, cyclohexadiene or ammonium formate, and wherein the ammonium formate is mixed with formic acid, and its conversion to paliperidone.
PCT/US2008/011433 2007-10-03 2008-10-02 Process for the synthesis of cmhtp, a paliperidone intermediate WO2009045489A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US99775507P 2007-10-03 2007-10-03
US60/997,755 2007-10-03

Publications (2)

Publication Number Publication Date
WO2009045489A2 WO2009045489A2 (en) 2009-04-09
WO2009045489A3 true WO2009045489A3 (en) 2009-05-22

Family

ID=40342389

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/011433 WO2009045489A2 (en) 2007-10-03 2008-10-02 Process for the synthesis of cmhtp, a paliperidone intermediate

Country Status (1)

Country Link
WO (1) WO2009045489A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2625323T3 (en) 2008-05-29 2017-07-19 Inke, S.A. Process to prepare paliperidone and intermediates thereof
ATE544766T1 (en) 2009-07-13 2012-02-15 Krka METHOD FOR SYNTHESIS OF PALIPERIDONE

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368388A2 (en) * 1988-11-07 1990-05-16 Janssen Pharmaceutica N.V. 3-Piperidinyl-1,2-benzisoxazoles
WO2008021345A2 (en) * 2006-08-14 2008-02-21 Teva Pharmaceutical Industries Ltd. Process for the synthesis of 9-hydroxy risperidone (paliperidone)

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368388A2 (en) * 1988-11-07 1990-05-16 Janssen Pharmaceutica N.V. 3-Piperidinyl-1,2-benzisoxazoles
WO2008021345A2 (en) * 2006-08-14 2008-02-21 Teva Pharmaceutical Industries Ltd. Process for the synthesis of 9-hydroxy risperidone (paliperidone)

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DE SMET K ET AL: "Selectivity Control by Use of Near-IR for a Hydrogenation Process", ORGANIC PROCESS RESEARCH AND DEVELOPMENT,, vol. 9, no. 3, 1 January 2005 (2005-01-01), pages 344 - 347, XP002477069 *
FÜLÖP F ET AL: "Synthesis of Partially Saturated Dipyrido[1,2-a:4,3-d]pyrimidin-11-ones Via Catalytic Hydrogen-Transfer Reaction", TETRAHEDRON, vol. 43, no. 6, 1987, pages 1157 - 1160, XP002515876 *
JOHNSTONE R A W ET AL: "Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds", CHEMICAL REVIEWS, ACS,WASHINGTON, DC, US, vol. 85, 1 January 1985 (1985-01-01), pages 129 - 170, XP002182953, ISSN: 0009-2665 *

Also Published As

Publication number Publication date
WO2009045489A2 (en) 2009-04-09

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